US2017369492A1PendingUtilityA1
1,3-substituted 2-amino-indole derivatives and analogues useful in the treatment or prevention of diabetes mellitus, obesity, and inflammatory bowel disease
Est. expiryJun 25, 2034(~7.9 yrs left)· nominal 20-yr term from priority
A61P 3/10A61P 43/00A61P 3/04A61K 31/437C07D 471/04A61K 31/5025C07D 487/04A61K 31/55C07D 519/00A61K 31/4985A61K 31/541A61K 31/5377C07D 401/02A61K 31/519A61P 1/04C07D 403/02
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Claims
Abstract
The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein Q, X 4 , X 5 , X 6 , X 7 , R 1 , R 2 , R 3 and R 8 are as defined in the specification, processes for the preparation of such compounds, pharmaceutical compositions containing them and the use of such compounds in therapy.
Claims
exact text as granted — not AI-modified1 . A compound of formula (I):
or a pharmaceutically acceptable salt thereof, wherein
Q represents —O—, —S—, —SO—, —SO 2 —, —SO 2 NR—, —SO 2 (CH 2 ) m — or —SO 2 O—;
R represents a hydrogen atom or a C 1 -C 6 alkyl group;
m is 1 or 2;
X 4 represents N or CR 4 ;
X 5 represents N or CR 5 ;
X 6 represents N or CR 6 ;
X 7 represents N or CR 7 ;
provided that one or two of X 4 , X 5 , X 6 and X 7 represents a nitrogen atom;
R 1 and R 2 each independently represent a hydrogen atom or a C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl or C 1 -C 6 alkoxycarbonyl group, each of which may be optionally substituted by at least one halogen atom;
R 3 represents a saturated or unsaturated 3- to 10-membered ring system which may comprise at least one ring heteroatom independently selected from nitrogen, oxygen and sulphur, wherein the 3- to 10-membered ring system is optionally substituted by at least one substituent independently selected from halogen, hydroxyl, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 6 cycloalkylC 1 -C 6 alkoxy, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 alkylC(O)NR 14 —, phenyl, (halo)phenylcarbonyl, phenoxy, benzyl, benzyloxycarbonyl and a saturated or unsaturated 4- to 6-membered heterocyclyl group, which heterocyclyl group is itself optionally substituted by at least one C 1 -C 6 alkyl group,
and when Q represents —SO 2 NR—, R 3 may additionally represent a C 1 -C 6 alkyl group optionally substituted by at least one substituent independently selected from halogen, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, phenyl and a saturated or unsaturated 4- to 6-membered heterocyclyl group;
R 4 , R 5 and R 6 each independently represent a hydrogen or a halogen atom, or a C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkyl, NR 12 R 13 , C 3 -C 8 cycloalkyl or C 5 -C 8 cycloalkenyl group;
R 7 represents a hydrogen or a halogen atom, hydroxyl, cyano, NR 9 R 10 , or a C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 6 alkenyl, C 5 -C 8 cycloalkenyl, C 1 -C 6 alkoxy, C 3 -C 8 cycloalkyloxy, benzyloxy, 3-to 11-membered saturated heterocyclyl, 3-to 11-membered saturated heterocyclyloxy, C 6 -C 10 aryl or heteroaryl group, each of which may be optionally substituted by at least one substituent independently selected from halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 8 cycloalkyl, phenyl and a saturated or unsaturated 4- to 6-membered heterocyclyl group wherein each C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 8 cycloalkyl, phenyl or saturated or unsaturated 4- to 6-membered heterocyclyl substituent group may itself be optionally substituted by at least one substituent independently selected from halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy and C 3 -C 6 cycloalkyl;
either R 8 represents a saturated 3- to 8-membered ring system which may comprise at least one ring heteroatom independently selected from nitrogen, oxygen and sulphur, wherein the 3- to 8-membered ring system is optionally substituted by at least one substituent independently selected from halogen, hydroxyl and C 1 -C 6 alkyl, or R 8 represents a C 1 -C 6 alkyl group optionally substituted by at least one substituent independently selected from phenyl and C 3 -C 6 cycloalkyl, the cycloalkyl group itself being optionally substituted by at least one C 1 -C 6 alkyl group;
R 9 and R 10 each independently represent a hydrogen atom, or a C 1 -C 6 alkyl or —(CH2) p —R 11 group, each of which may be optionally substituted by at least one substituent independently selected from halogen, C 1 -C 3 alkyl and C 1 -C 3 alkoxy;
p is 0 or 1;
R 11 represents C 3 -C 6 cycloalkyl, phenyl or a saturated or unsaturated 5- to 6-membered heterocyclyl group; and
R 12 , R 13 and R 14 each independently represent a hydrogen atom or a C 1 -C 6 alkyl group.
2 . A compound according to claim 1 , wherein X 4 and X 7 are N, X 5 is CR 5 and X 6 is CR 6 .
3 . A compound according to claim 1 , wherein X 4 and X 6 are both N, X 5 is CR 5 and X 7 is CR 7 .
4 . A compound according to claim 1 , wherein Q represents —SO 2 —.
5 . A compound according to claim 1 , wherein R 1 and R 2 are both hydrogen.
6 . A compound according to claim 1 , wherein R 3 represents a saturated or unsaturated 3- to 10-membered ring system which may comprise at least one ring heteroatom independently selected from nitrogen, oxygen and sulphur, optionally substituted as defined in claim 1 , wherein the ring system is selected from phenyl, thienyl, cyclopropyl, cyclohexyl, pyridinyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, azetidinyl, 1,4-oxazepanyl, azepanyl, thiomorpholinyl, 1,2,3,4-tetrahydroisoquinolinyl, 2,3-dihydroisoindolyl, azabicyclo[3.2.1]octanyl and 2,3-dihydro-1,4-benzodioxinyl.
7 . A compound according to claim 1 , wherein R 3 represents phenyl optionally substituted by one or two substituents independently selected from fluorine, chlorine, cyano, methyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy and C 1 -C 3 alkoxy.
8 . A compound according to claim 1 , wherein R 8 represents a saturated 4- to 7-membered ring system which may comprise at least one ring heteroatom independently selected from nitrogen, oxygen and sulphur, wherein the 4- to 7-membered ring system is optionally substituted by at least one substituent independently selected from halogen, hydroxyl and C 1 -C 2 alkyl, or R 8 represents a C 1 -C 2 alkyl group optionally substituted by at least one substituent independently selected from phenyl and C 3 -C 6 cycloalkyl, the cycloalkyl group itself being optionally substituted by at least one C 1 -C 2 alkyl group.
9 . A compound according to claim 1 , wherein R 8 represents a C 4 -C 6 cycloalkyl group optionally substituted by at least one substituent independently selected from fluorine, hydroxyl and methyl.
10 . A compound according to claim 1 , selected from the group consisting of:
7-(benzenesulfonyl)-5-cyclohexyl-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cycloheptyl-7-[(4-methylbenzene)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cycloheptyl-7-[(4-methylbenzene)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclopentyl-7-[(4-methylbenzene)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-6-amine, 7-[(4-chlorobenzene)sulfonyl]-5-cyclohexyl-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-[(4-fluorobenzene)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-{[4-(propan-2-yloxy)benzene]sulfonyl}-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-(thiophene-2-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 3-(benzenesulfonyl)-1-cyclohexyl-1H-pyrrolo[3,2-b]pyridin-2-amine, 1-cyclopentyl-3-[(4-methylbenzene)sulfonyl]-1H-pyrrolo[3,2-b]pyridin-2-amine, 1-cyclohexyl-3-[(4-methylbenzene)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-2-amine, 7-(cyclohexanesulfonyl)-5-cyclohexyl-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-(4,4-difluorocyclohexyl)-7-[(4-methoxybenzene)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-6-amine, 1-(4,4-difluorocyclohexyl)-3-[(4-methoxybenzene)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-2-amine, 3-(benzenesulfonyl)-1-cyclohexyl-1H-pyrrolo[2,3-b]pyridin-2-amine, 3-(benzenesulfonyl)-1-cyclohexyl-1H-pyrrolo[2,3-b]pyridin-2-amine, 3-(benzenesulfonyl)-1-(4,4-difluorocyclohexyl)-1H-pyrrolo[2,3-b]pyridin-2-amine, 7-(benzenesulfonyl)-5-cyclohexyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine, 3-(benzenesulfonyl)-1-cyclohexyl-1H-pyrrolo[2,3-c]pyridin-2-amine, 3-(benzenesulfonyl)-1-(4,4-difluorocyclohexyl)-1H-pyrrolo[3,2-b]pyridin-2-amine, 1-(4,4-difluorocyclohexyl)-3-[(4-methoxybenzene)sulfonyl]-1H-pyrrolo[3,2-b]pyridin-2-amine, 3-(benzenesulfonyl)-1-cyclohexyl-1H-pyrrolo[3,2-c]pyridin-2-amine, methyl N-[7-(benzenesulfonyl)-5-cyclohexyl-5H-pyrrolo[2,3-b]pyrazin-6-yl]carbamate, 3-(benzenesulfonyl)-1-(4,4-difluorocyclohexyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-2-amine, 7-(benzenesulfonyl)-5-cyclohexyl-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-6-amine, 5-(benzenesulfonyl)-3-chloro-7-cyclohexyl-7H-pyrrolo[2,3-c]pyridazin-6-amine, 5-(benzenesulfonyl)-7-cyclohexyl-7H-pyrrolo[2,3-c]pyridazin-6-amine, 7-(benzenesulfonyl)-5-(4,4-difluorocyclohexyl)-4-ethoxy-5H-pyrrolo[3,2-d]pyrimidin-6-amine, 7-(benzenesulfonyl)-4-(benzyloxy)-5-(4,4-difluorocyclohexyl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine, 6-amino-5-(4,4-difluorocyclohexyl)-7-(phenylsulfonyl)-5H-pyrrolo[3,2-d]pyrimidin-4-ol, 7-(benzenesulfonyl)-4-chloro-5-(4,4-difluorocyclohexyl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine, 7-(benzenesulfonyl)-5-(4,4-difluorocyclohexyl)-4-N-methyl-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine, 7-(benzenesulfonyl)-5-cyclohexyl-4-N,4-N-dimethyl-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine, 7-(benzenesulfonyl)-5-cyclopentyl-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-6-amine, 3-(benzenesulfonyl)-1-cyclohexyl-7-methoxy-1H-pyrrolo[2,3-c]pyridin-2-amine, 6-amino-7-(benzenesulfonyl)-5-cyclohexyl-5H-pyrrolo[3,2-d]pyrimidine-carbonitrile, 5-cyclohexyl-7-(2-fluorobenzenesulfonyl)-4-methoxy-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine, 5-cyclohexyl-7-(3-fluorobenzenesulfonyl)-4-methoxy-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine, 7-(benzenesulfonyl)-4-methoxy-5-(oxan-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine, 6-amino-5-cyclohexyl-N-phenyl-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide, 6-amino-5-cyclohexyl-N-(pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide, 5-cyclobutyl-7-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-(2-methylcyclohexyl)-7-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-butyl-7-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-phenethyl-7-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 2-(6-amino-7-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-5-yl)cyclohexanol, 5-(2-cyclopropylethyl)-7-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-(4,4-difluoro-cyclohexyl)-7-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-(2-cyclobutylethyl)-7-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 7-(phenylsulfonyl)-5-(tetrahydro-2H-pyran-3-yl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-(3,3-dimethylbutyl)-7-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-((1R*,2R*,4S*)-bicyclo[2.2.1]heptan-2-yl)-7-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-(cyclopentylmethyl)-7-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-((1-ethyl cyclopropyl)-methyl)-7-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-((2,2-dimethylcyclopropyl)methyl)-7-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-(piperidin-1-ylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-(pyrrolidin-1-ylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 6-amino-5-cyclohexyl-N-propyl-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide, 6-amino-5-cyclohexyl-N-methyl-N-propyl-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide, 5-cyclohexyl-7-(morpholinosulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-((4-methylpiperidin-1-yl)sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-((4-methylpiperazin-1-yl)sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-((3-methoxyazetidin-1-yl)sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-((4-ethoxypiperidin-1-yl)sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-((4,4-dimethylpiperidin-1-yl)sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-((3-methylpyrrolidin-1-yl)sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-((2-methylpyrrolidin-1-yl)sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-((4,4-difluoropiperidin-1-yl)sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 6-amino-N-benzyl-5-cyclohexyl-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide, 6-amino-N,5-dicyclohexyl-N-methyl-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide, 5-cyclohexyl-7-(1,4-oxazepane-4-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-(4-methoxypiperidine-1-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 6-amino-N-(cyclobutylmethyl)-5-cyclohexyl-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide, 5-cyclohexyl-7-(3,3-dimethylpyrrolidine-1-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-(2,6-dimethylmorpholine-4-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 7-(azepane-1-sulfonyl)-5-cyclohexyl-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-(thiomorpholine-4-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, N-(1-{6-amino-5-cyclohexyl-5H-pyrrolo[2,3-b]pyrazine-7-sulfonyl}piperidin-4-yl)-N-methylacetamide, 6-amino-5-cyclohexyl-N-(oxetan-3-ylmethyl)-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide, 7-(4-benzylpiperidine-1-sulfonyl)-5-cyclohexyl-5H-pyrrolo[2,3-b]pyrazin-6-amine, 6-amino-5-cyclohexyl-N-(3,3,3-trifluoropropyl)-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide, 5-cyclohexyl-7-(4-phenylpiperidine-1-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 6-amino-5-cyclohexyl-N-(2-phenylethyl)-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide, 5-cyclohexyl-7-(4-phenoxypiperidine-1-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-(3-phenylpyrrolidine-1-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-[4-(trifluoromethyl)piperidine-1-sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-[3-(methoxymethyl)pyrrolidine-1-sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-6-amine, 6-amino-5-cyclohexyl-N-(cyclopropylmethyl)-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide, 6-amino-5-cyclohexyl-N-(2-methoxyethyl)-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide, 5-cyclohexyl-7-(3-methoxypyrrolidine-1-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-(3,3-dimethylpiperidine-1-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 1-{6-amino-5-cyclohexyl-5H-pyrrolo[2,3-b]pyrazine-7-sulfonyl}piperidin-4-ol, 5-cyclohexyl-7-(1,2,3,4-tetrahydroisoquinoline-2-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 6-amino-N-(butan-2-yl)-5-cyclohexyl-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide, 6-amino-5-cyclohexyl-N-(oxolan-2-ylmethyl)-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide, 5-cyclohexyl-7-(2,3-dihydro-1H-isoindole-2-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-{4-[(4-fluorophenyl)carbonyl]piperazine-1-sulfonyl}-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-(3-phenoxyazetidine-1-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-[3-(piperidin-1-yl)azetidine-1-sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-[3-(1H-pyrazol-1-yl)azetidine-1-sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-(3-methylpiperidine-1-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 6-amino-5-cyclohexyl-N-[2-(1,3-thiazol-2-yl)ethyl]-5H-pyrrolo[2,3-b]pyrazine-7-sulfonamide, 8-{6-amino-5-cyclohexyl-5H-pyrrolo[2,3-b]pyrazine-7-sulfonyl}-8-azabicyclo[3.2.1]octan-3-ol, 5-cyclohexyl-7-[4-(2,2,2-trifluoroethyl)-piperazine-1-sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-6-amine, (1-{6-amino-5-cyclohexyl-5H-pyrrolo[2,3-b]pyrazine-7-sulfonyl}piperidin-4-yl)methanol, 5-cyclohexyl-7-[4-(cyclopropylmethoxy)piperidine-1-sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-[(4-methoxybenzene)-sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-(cyclopropanesulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-[(3-fluorobenzene)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-[(2-fluorobenzene)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-[(3-methoxybenzene)-sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-6-amine, 4-{6-amino-5-cyclohexyl-5H-pyrrolo[2,3-b]pyrazine-7-sulfonyl}benzonitrile, 7-[(3-chloro-4-methoxybenzene)-sulfonyl]-5-cyclohexyl-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-(6-methoxypyridine-3-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-{[4-(trifluoromethoxy)-benzene]sulfonyl}-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-(2,3-dihydro-1,4-benzodioxine-6-sulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-amine, 5-cyclohexyl-7-{[4-(difluoromethoxy)-benzene]sulfonyl}-5H-pyrrolo[2,3-b]pyrazin-6-amine, and pharmaceutically acceptable salts of any one thereof.
11 . A process for the preparation of a compound of formula (I) or a pharmaceutically acceptable salt thereof, as defined in claim 1 which comprises
(a) when NR 1 R 2 represents NH 2 , reacting a compound of formula
wherein L 1 represents a leaving group and X 4 , X 5 , X 6 , X 7 , Q and R 3 are as defined in formula (I), with a compound of formula (III), H 2 NR 8 , or a salt thereof wherein R 8 is as defined in formula (I); or
(b) when NR 1 R 2 represents NH 2 , reacting a compound of formula
wherein L 2 represents a leaving group and X 4 , X 5 , X 6 , X 7 and R 8 are as defined in formula (I), with a compound of formula
wherein Q and R 3 are as defined in formula (I);
wherein any of compounds (II), (III), (IV) or (V) may optionally be protected;
and optionally thereafter carrying out one or more of the following procedures:
removing any protecting groups
converting a compound of formula (I) into another compound of formula (I)
forming a pharmaceutically acceptable salt.
12 . A pharmaceutical composition comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof, as claimed in claim 1 , in association with a pharmaceutically acceptable adjuvant, diluent or carrier, and optionally one or more other therapeutic agents.
13 . (canceled)
14 . A method for treating a condition whose development or symptoms are linked to GPR43 receptor activity, comprising administering a compound of formula (I) as claimed in claim 1 or a pharmaceutically acceptable salt thereof.
15 . A method for treating obesity and/or diabetes, comprising administering a compound of formula (I) as claimed in claim 1 or a pharmaceutically acceptable salt thereof.
16 . A method for treating inflammatory bowel disease, comprising administering a compound of formula (I) as claimed in claim 1 or a pharmaceutically acceptable salt thereof.Join the waitlist — get patent alerts
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